15 Most Despicable Things The Simpsons' Mr. Burns Has Ever Done

The Simpsons is the longest running show on television (sitting at 28 seasons) and has offered humor that can reach a wide array of audiences for most of that time. From ludicrous episodes like You On

The Simpsons is the longest running show on television (sitting at 28 seasons) and has offered humor that can reach a wide array of audiences for most of that time. From ludicrous episodes like You Only Move Twice, when Homer is employed by a James Bond-esque villain, Hank Scorpio, to iconic ones like Homer at the Bat and The City of New York VS Homer Simpson, the yellow family has done it all and while the show as we see it today is not like it used to be ('member seasons three to seven? Yeah, I 'member, sorry that's a South Park joke in a Simpsons article), it is still worth a watch.

A large part of what gives The Simpsons its charm is that it boasts one of the most likable villains in the history of fictional bad guys. Charles Montgomery Burns (voiced by Harry Shearer, who almost quit last year) is so vile and so evil that audiences can't help but laugh at his absurd misanthropy, elitism and pure, vile repugnance. Every now and again, ol' Burnsie gets humanized but more often than not he is the embodiment of the evil businessman, and the embodiment of greed.

Looking at him, he bears a striking resemblance to Jacob Rothschild, but series creator Matt Groening, has said that Monty is based on a teacher he had in his youth, but that a couple of members of the Rockefeller oil family also served as inspirations for the series' most consistent antagonist. Earlier we mentioned how much of a comically evil character he is, and with that in mind, we've compiled a list of his most over-the-top evil moments. If we missed anything, let us know in the almighty comments section. We do however, think you'll find the list... excellent.

15 Trying To Seal Homer Inside A Crypt


There are a few times throughout the series in which Mr. Burns tries to murder someone. As we'll see (and as you all know if you're fans) he's a complete psychopath who will do absolutely anything to get what he wants and satisfy any grudge, no matter how menial.

The fourteenth season episode C.E.D'oh, Homer uses a clever trick to take over power of the nuclear plant from Burns, firing him upon the completion of this task. Burns and assistant Waylon Smithers, go on a vacation to Morocco while Homer gradually realizes that life as the man in charge isn't all that it is cracked up to be.

Upon Burns' return, Homer has become disenchanted due to poor work/life balance, and is ready to turn leadership of the plant back over to Burns, but as Monty walks Homer through a cemetery (to show Homer where he'll end up if he keeps ignoring his family), Burns drugs Homer in an empty crypt and attempts to close off the entry, immuring him. Fortunately, Burns is notoriously weak and can barely lift bricks, and thus his project takes so long, the drugs wear off and Homer walks away. Sure this plan didn't get accomplished, but the evil intent was there.

14 He Engineered Bioweapons

We know very little about Mona Simpson's life. She is Homer's mother obviously, but she has lived much of her life on the run and has been in just a few (granted, very memorable) episodes. The first of these was the aptly named Mother Simpson. We learned that Mona left Abe after she became a hippy, having been turned from her former conservative ways by the sight of Joe Namath's hair (while Abe was critical of Namath's attitude and hair, calling Johnny Unitas' hair a cut you "could set your watch to").

After she started her years as a hippy, one of her first politically charged activities was to attack and destroy Monty Burns' biological weapons lab. I hope we don't have to explain why operating such a lab is a bad thing.

13 Harassing Marge

Back in season four, Marge got a job with the nuclear plant after the Simpsons discovered that their home had a significantly damaged foundation. Burns became enamored with her and tried to turn on the charm. He was subtle and kind at first, but ultimately, trying to pursue a married woman is a problem. But where it really became despicable was when Burns went into full-on creep mode. He was in the middle of firing Marge because she refused to become romantically involved with him, and she said she would "sue the pants off" him. The old man responded with an awkward gem: "you don't have to sue me to get my pants off". Not cool, that's right up there with "grab 'em by the... blue hair".

12 Lil' Lisa's Patented Animal Slurry

Back in season eight, all of The Simpsons fandom partook in some schadenfreude (pleasure at the misery of another) when Burns went completely broke. In the wake of his bankruptcy, Lisa taught him about recycling (re-cy-cling?). Her example of why recycling was so important was to show him a fish caught in a six-pack holder. Burns, being the business-minded entrepreneur that he is, found a way to make recycling profitable, creating a massive web of six pack holders that could take all manner of aquatic wildlife to be turned into Lil' Lisa Slurry; which could be used to feed livestock, cool engines, and as a substitute for dynamite.

Disgusted, Lisa informs Burns that he is not only an evil man, but when he tries to do good he is even more evil.

11 Crippling The Irish Laborer With His Bumper Car

In the fifth season episode entitled $pringfield (or, How I Learned to Stop Worrying and Love Legalized Gambling), the town was in decline so Mayor Quimby and the townsfolk decided to legalize gambling and build a casino to stimulate the economy. Of course this is the episode in which Bart starts his own casino in his treehouse and Marge develops a gambling addiction. Actually, she was just enslaved by a gambling monster; Gamblor.

Early on in the episode, Burns and Quimby walk along the town's boardwalk and Burns recalls his youth, particularly an incident in which he repeatedly ran a bumper car into a blue collar Irish laborer as the man cried out in pain. Burns laughed hysterically as a child and upon remembering this, he laughed for days. "What was I laughing at? Ah yes that crippled Irishman".

Taking sick pleasure in another person's suffering is a pastime for Burns.

10 Keeping The Trillion Dollar Bill (And giving It To Fidel Castro)

In the world of The Simpsons, President Harry Truman sent a trillion dollar bill to postwar Europe to help rebuild American allies who "fought so poorly and surrendered so readily" during World War II. The pilot: none other than Springfield's own C. Montgomery Burns, the wealthiest, and therefore most trustworthy citizen. Of course, he kept the money for himself and it never arrived in Europe. The European leaders hoping to put that money to good use then vowed to be snooty to Americans forever. This is Burns' fault.

Later in the episode, with the IRS hot on their trail, Homer, Burns and Smithers escape America and land in Cuba. In a meeting with Fidel Castro, Burns hands him the trillion dollar bill to examine, at which point the dictator steals it. "Give what back?". Never trust a commie.

9 Stealing Oil From The School

Burns' greed knows no bounds. In season seven, the two-part episode Who Shot Mr. Burns told the story of the time when Springfield Elementary struck oil. Of course, Springfield's wealthiest citizen wouldn't allow that amount of money to be controlled by a public entity like a school, so he did what he had to do to steal the profit for himself. That was the slant drilling operation. This infuriated the entire town.

The key figures in the school had already decided what they wanted to do with the money. Lisa wanted to hire musician Tito Puente to teach, Otto wanted "those guitars that are like, double guitars", and Groundskeeper Willie wanted a crystal slop bucket. These requests were granted, but then stripped away by Burns' greed. Most heinous of all however, was when the fumes from the oil rig caused the closure of Moe's Tavern. "Man alive! There are... men, alive in here!"

8 Leaving His Parents

Rosebud was the fifth season episode that tells the story of Burns' stuffed bear Bobo. He abandoned the bear as a child, and it made its way around the world, from Nazi Germany to the arctic and several other points in between. Bobo eventually ended up back in Springfield and was purchased with a bag of ice (a head bag, chock full of... heady goodness) and brought home to the Simpson household. Early in the episode however, we see the first evil thing Burns did. He was a happy, carefree child, playing around his family home with his parents when a "loveless billionaire" rolled up and offered to take the boy. When his loving parents explained the situation, he hopped in the car without a moment's thought abandoning his family.

7 Hitting Bart With His Car (And Not Caring)

Way back in 1991 during season two, in the simply named episode Bart Gets Hit By a Car, Bart Simpson is stuck by a vehicle driven by Monty. Despite some initial panic, Bart escapes with significant injuries but nothing life threatening. The episode centers on the resulting court case and whether or not Marge is willing to bend the truth in order to get a hefty settlement out of Burns. Being as honest as she is, they end up getting nothing, but in the end, everything works out and there is no animosity between Homer and Marge. This was also the first appearance of the wacky ambulance chaser, Lionel Hutz.

While Burns' act of hitting Bart with his vehicle can be considered an accident, when Smithers exits the car to examine Bart's injuries, Burns doesn't care one bit and says: "Oh for crying out loud, give him a nickel and let's get going!".

6 Dumping Nuclear Waste In The Park

Marge vs the Monorail is one of the most memorable episodes in the entire series, with a catchy song (the monorail song, of course), a few great gags (such as Bart turning into an anchor while the train is speeding along the track, "think harder Homer"), and a funny, albeit brief cameo by Leonard Nimoy.

The episode begins with power plant workers Lenny Leonard and Carlson, sealing up a drum of nuclear waste at the plant. They finish their task and leave. Smithers and Burns walk in with a dolly and decide not to dump their waste in the school this time (all the bald children are arousing suspicion) and instead head off to the park. While cramming barrels of waste into the trees in the local park, we see a tree with tentacles and a mutated squirrel with laser eyes and a frog-like tongue emerge to eat an acorn.

Now I'm no environmental activist, but Burns' willingness to dump incredibly harmful substances into areas frequented by children is a pretty evil move.

5 He Tried To Kill His Mother

At the start of Homer the Smithers, in season seven, Waylon Smithers suffers a sort of nervous breakdown after Burns becomes terrified at Lenny during a company outing (Lenny was just intoxicated and trying to thank Burns for a fun evening). Burns eventually instructs Smithers to take a vacation, and Smithers chooses Homer to be Burns' assistant during his absence, seeking someone who won't overshadow his work ethic and effectiveness. While preparing Homer for the job, Burns' mother calls. She's 122 years old and is so decrepit that all she can do is sit in her rocking chair, dial a phone and scream, usually at her son. We then find out that decades prior, Burns had tried to kill his mother by pulling the plug on her, not expecting her to pull through and live for another several decades. It was also suggested that his reason for doing so was to exact revenge on her for having an affair with former President William Howard Taft.

4 Attempting To Make Clothing Out Of Puppies

There have been some catchy tunes in the 28 years of The Simpsons. The closing song from Homer at the Bat comes to mind, as does the Mr. Plow tune (and the Plow King ad for that matter), but "See My Vest", sung to the tune of Beauty and the Beast's "Be Our Guest" is probably the best and funniest.

While they made light of the idea very well, the thought of using puppy fur to make a suit is pretty awful. Using fur for clothing is somewhat controversial to begin with these days, but the thought of using a beloved domesticated pet is particularly nasty, even to those of us who could care less about animals.

Thankfully, Burns never did kill these puppies and instead raised them to race, earning a pile of money. Homer was less than pleased.

3 Blocking Out The Sun

Another despicable event from Who Shot Mr. Burns occurred when the old man devises a plan to use a large mechanical disk to completely block the sunlight from getting to Springfield, which in turn would see the townspeople required to use Burns' electricity to light everything.

Aside from being a nasty and selfish move from a financial standpoint, this would have disastrous effects on the city. The sun is a primary source from where people get vitamin D, not to mention all the other stuff it does. There is a reason people in ancient times worshiped the thing. I don't need to tell you why the sun is important. This is far worse than the slanted oil well under the school, but not as bad as the next couple of incidents.

2 Shutting Off The Power To The City

Season four saw the nuclear plant workers strike against management in response to the cancellation of the dental plan. Of course, in the same episode, Marge and Homer were told that Lisa would need braces to correct the growth of her teeth. Initially, Burns would not budge, and Homer, as head of the union, had all of his co-workers outside of the plant singing protest songs and picketing.

To try to break the strike, Burns finally turned off all the power in the city. In such an event, with the dependence that any city has on electricity, there would be near absolute chaos. Traffic lights would not work, causing accidents, anyone relying on hospital systems would be in jeopardy (depending on backup generators, but Springfield isn't a huge town). Anyway, you get the idea, this is a nasty and despicable act that Burns used to screw the entire city over his own quarrel with his workers.

1 Trying To Kill Bart And Abe

Sorry, we had to use this picture because it is possibly the funniest gag in a pretty great episode. Possibly the only decent thing Monty Burns did in his life was fight in World War Two. With that said, he spent much of his time avoiding the fight, and being a drain on his unit. Burns even wrecked Abe's opportunity to shoot Hitler. This all took place in season seven's classic Raging Abe Simpson and His Grumbling Grandson in "The Curse of the Flying Hellfish. 

While clearing out some old buildings after a battle, the Flying Hellfish (as their unit was known), found some valuable works of art. Knowing that it was a crime to take valuables for their own, the group entered into a tontine, whereby the last member of the agreement alive would take ownership of the artwork.

Burns and Grandpa Simpson end up being the last two alive, and Burns tries to have Abe killed. After his assassin fails several times, Burns just demolishes part of the Simpson's house and extorts the key to the art from Grandpa. Bart gets the key back with some clever slight of hand, and they try to reach the box which is at the bottom of the sea. Burns catches up however, and when he arrives on the boat, he tries to kill both Bart and Grandpa. Of course he failed, but just trying to kill a small boy and his grandfather (Burns' unit commander) gets him kicked out of the tontine and unit. Of course, Grandpa is never allowed to take possession of the artwork and it is returned to the descendant of the German who was stolen from.

Sources: No Homers, Uproxx, Hitfix, Dorkly, The Simpsons Wikia, YouTube

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15 Most Despicable Things The Simpsons' Mr. Burns Has Ever Done